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■ Synthesis and Reactivity of Dibenz[d,g]azecin-14(5H)-ones

Patrick Mohr, Jochen Lehmann, and Michael Decker*

*Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University of Jena, Philosophenweg 14, D-07743 Jena, Germany

Abstract

Ring cleavage of the central C,N-bond in quaternary dibenz[a,h]quinolizinium salts with sodium hydride in DMSO yielded novel dibenz[d,g]azecin-14(5H)-ones, which produce cyclic carbinolamine derivatives in an acidified medium by transannular interaction. Investigations into the optimization of the NaH/DMSO reaction as ring cleaving reaction were performed. The ketone moiety of the azecinones is remarkably stable towards different reductive agents most probably due to steric hindrance, because also the quaternary ammonium salts which are unable to recyclize to carbinolammonium salts could not be reduced either. The compounds were screened for their affinity to hD₁-, hD₂- and hD₃-receptor subtypes, but did not show significant affinity in strong contrast to analogues without the ketone moiety.